Diethyl Pyrocarbonate

HCID 3051
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Basic information

CAS
1609-47-8
Standard SMILES
CCOC(=O)OC(=O)OCC
InChIKey
FFYPMLJYZAEMQB-UHFFFAOYSA-N
Molecular formula
C6H10O5
Average molar mass
162.14 g/mol
Monoisotopic mass
162.05282342

Overview

Diethyl pyrocarbonate is the diethyl ester of dicarbonic acid. It is functionally related to a dicarbonic acid.

Names & identifiers

Preferred name
Diethyl Pyrocarbonate
IUPAC
ethoxycarbonyl ethyl carbonate
English name
Diethyl pyrocarbonate
Molecular formula
C6H10O5
Molecular weight
162.14

Names & synonyms

diethyl pyrocarbonate1609-47-8Diethyl dicarbonateDEPCDiethyl oxydiformateDiethylpyrocarbonateBaycovinEthyl pyrocarbonatePirefDicarbonic acid, diethyl esterDicarbonic acid diethyl esterDiethyl pyrocarbonic acid
Show more names
ethoxycarbonyl ethyl carbonateDKDDEP／DEPCDEPC/DEPethylpyrocarbonate
Oxydiformic acid diethyl esterPyrocarbonic acid diethyl esterDiethylpyrokarbonatEthoxyformic acid anhydridePyrocarbonate d'ethylePyrokohlensaeure diaethyl esterDiethyl ester of pyrocarbonic acidDiethylester kyseliny diuhlicite

Database identifiers

CAS
1609-47-8
PubChem CID
3051
DTXSID
DTXSID2051764
ChEMBL
CHEMBL55517
ChEBI
CHEBI:59051
UNII
LMR3LZG146
EC Number
216-542-8
Nikkaji
J13.055I

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
61.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
6
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Esters, Other
Food AdditivesDOUGH STRENGTHENER -> FDA Substance added to food
Density1.12 @25 °C
Melting Point< 25 °C
Physical Description · 2 items

Viscous liquid with a fruity odor. [Merck Index] Clear colorless liquid; [Sigma-Aldrich MSDS]

Solid

Physicochemical properties

Melting point
69 ℃ · 69℃
Boiling point
93 · 93-94 °C18 mm Hg(lit.)
Density
1.12 g/mL · 1.12 g/mL at 20 °C
refractive index
20 · n20/D 1.398(lit.)
Flash point
157 °F · 157 °F
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (93.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 93 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Dicarbonic acid, diethyl ester

Diethyl dicarbonate: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Causes dyspnea in inhalation lethal-concentration studies of guinea pigs, mice, and rabbits (LCLo = 10 ppm/1hr); [RTECS] Slowly decomposed by water forming ethanol and carbon dioxide; A skin, eye, and mucous membrane irritant; [Merck Index] A skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesAcute Tox. 4 (93.5%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

4.1 [mg/m3]

45 [mg/m3]

270 [mg/m3]

Toxicology

Toxicity DataLCLo (rat) = 10,000 mg/m3/1hr

Safety data

F
4.4-9-21
wgk
3
tsca
TSCA listed
rtecs
LQ9350000
ridadr
2810
hs_code
29209085

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 2 items

Used as a preservative in wines, soft drinks, and fruit juices; [Merck Index] Used as a laboratory reagent; [REPROTOX]

Banned for use as a food additive; [FDA]

Use ClassificationFood Additives -> PRESERVATIVE -> JECFA Functional Classes
General Manufacturing InformationDicarbonic acid, 1,3-diethyl ester: ACTIVE
Applications · 4 items

UsesModification reagent for His and Tyr residues in proteins. Robust probe for structural disruptions in dsDNA, reacting with fully or partially unstacked bases.1

UsesDiethyl pyrocarbonate may be used in the following studies:For the modification of histidyl residues in proteins.As a nuclease inhibitor, for the extraction of undegraded nucleic acids from etiolated and green plant tissues.For the modification of linear and supercoiled plasmid DNAs.As a chemical probe to investigate the secondary structure in negatively supercoiled DNA.For cabethoxylation of histidine residues of actin.

UsesGentle esterifying agent. Preservative for wines, soft drinks, fruit juices.

General DescriptionDiethyl pyrocarbonate (DEP) is a bactericidal agent and decomposes in water to CO2 and ethanol. DEP inhibits enzymes such as DNase and RNase without affecting nucleic acids. It is useful for the preparation of mRNA from tissues.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
清宁生物（江苏博泉生物科技有限公司）19352250998 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

DefinitionChEBI: The diethyl ester of dicarbonic acid.

Related reactions

130 records
New reaction record

Compound notes

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